Meeting Them - Teen!Dean x Teen!Reader

First Enemy

School went as normal as any could. Second period was more exciting, though. The teacher pulled you and Dean aside like he promised, then brought up Sam. "You've been accepted into the advanced program. You three are probably the smartest kids in the building right now, so you'll be alone in all your classes except for the extracurriculars. Today is gym for you guys, but I'll lend you some clothes since you didn't know. (Y/n) and Dean, I'd be glad to personally tutor you in some higher science if you'd like. Biology for humans, mostly," he offered. Dean looked disgruntled at the best, but you and Sam were beaming. "I don't think--" You stomped on Dean's foot and he shot you a dark glare. "Can Sam come? He's not as ahead as Dean and I, but I can help him catch up. It'd be good for what we do with our fathers do," you requested. Sam nodded and the teacher agreed. You put your arm around Sam and shook him lightly. He grinned, but Dean groaned. "Dean, if you even want a chance, cram it. I've put some thought into it, so shhh unless you want me to change my mind," you muttered. He straightened up as you walked back into the room. 

"Where are you going?" asked Jo quietly. "I made it into the advanced classes, so I have to leave. We'll still have art together and the bus ride, okay? You're the bae, Jo. Love ya, girlie," you said with a wink. She seemed down, but smiled. Mr. Novak motioned for you three to follow him and you did. "Aw, angel face is leaving," snickered a boy as you walked by. Dean wrapped an arm around you and pulled you close to him. You sighed, but let him do his thing. "Yeah, she is an angel face, ain't she?" said Dean with a raised eyebrow. The boy muttered something and you had to practically drag Dean out before he punched the kid. 

The room was small, and you meant SMALL. Five desks, including the one for the teacher, filled up the whole room. You slid into the first one and the boys took the ones on either side of you. Mr. Novak left and an elderly woman came in to replace him. "Which one of you is Sam? I'm assuming you're (Y/n)," she started. Sam raised his hand and she nodded. "So you're Dean, the troublemaker," she continued. He smirked and began to nod, but you gave him a look of desperation and his face softened. "No, ma'am, I will try my best to behave," he said. You smiled and squeezed his hand before letting it go. She nodded approvingly and began with calculus. Sam actually understood it, as did you and Dean. She was shocked at what you already knew and started to go higher and higher. Sam's eyes were ablaze every time she gave him new information and Dean smirked at every compliment. "You boys are geniuses," you whispered. Sam blushed furiously at this and Dean grinned. "Not as much as you, baby," he said. "Not your baby yet, Dean. Just wanted to see what you'd do. I liked it, by the way," you returned. "Please, God, make them stop flirting," mumbled Sam and you turned your attention back to the board. Soon after was lunch with the rest of the school.

Dean and Sam stood close to you walking in, but no one seemed to notice you but Jo. "(Y/n)! Bring them and come over here!" she yelled over the racket. You looked to them and they shrugged in unison. You smiled and pulled them forward by their hands. Jo sat across from you and the boys on either side. Other girls were staring in shock at Dean's placement and the seemingly new kid. "Jo Harvelle," said Jo shyly, sticking out a hand. "I'm Dean Winchester, that's my little brother, Sam," he introduced. He flashed his signature smile and she turned a deep scarlet. After that, it went rather smoothly. Sam was fascinated by her drawings and you three talked contently until someone popped up behind Dean. 

She tapped him on the shoulder and he spun around. She was gorgeous, with long blonde hair, shining blue eyes, tan, unmarred skin and a bit too much skin showing. Smiling a shy smile, she said, "Hi, Dean. I'm Sylvia Prince. You should really ditch these losers and come with me and my friends. We have you in best interest, Dean," she said, laying a perfectly manicured hand on his broad shoulder. You knew you couldn't compete with her and waited for him to get up and move. "You know," he said, moving her hand, "one of 'these losers' is my brother, and the other one is my girlfriend, who is better than you'll ever be. I think Jo's pretty cool, too. They  have me in best interest, Miss Prince." Her jaw fell open and she just stood there. "Scamper," he said, and she shot you a glare. "You'll lose him and I'll be there, freak," she said viciously. "Oh, sweetheart, I'd like to see you try. I wouldn't even break a nail slapping that face. Don't try me, prep. I could rip you in half with one hand," you teased. She stomped her foot and stormed away. The entire cafeteria burst into applause and you were taken aback. You didn't know they were watching. Sam pulled you down and Jo was grinning. "So... new boyfriend, hate the most popular girl in school, anything else you wanna share with the class?" she said with a laugh. You glanced over at Dean and smiled before slipping your small hand into his large one. His grip tightened and you said, "Nope. I'd tell you, girlfriend."

Needless to say, the fun wouldn't end there.